The Longest Day
by AngelGirl569
Summary: Arnold and Lila are Hillwood's most adored couple. The golden boy and the perfect girl. But when forced to confront the future, Arnold finds himself questioning both their relationship and himself. Can their story end happily, or is it time to end it?
1. The Longest Day

**A Hey Arnold story that takes place in the span of one day. Character descriptions are in chapter two as I didn't want to waste a bunch of space describing clothes, piercings, hair styles, etc. so if you want to get an idea of what the characters are like visually, go to chapter two before reading the story.**

 **When reading Hey Arnold stories, I notice that Lila is often cast as a bitch or a slut, even though in the actual show Lila is very sweet, kind, and innocent. People just like to vilify her as an excuse for why Arnold isn't interested in her anymore. But keeping Lila in character, at some point I figure Arnold would have to win her over. This story picks up after they have been dating for two years. The gang are in their senior year, and it's time to start thinking seriously about their futures.**

 **Enjoy the story! Leave reviews!**

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"So Arnold," Gerald said casually. He kept one hand on the wheel of his convertible, and one hand on the armrest, fingers poised to crank the tunes when the time came. The first of the gang to get a car, Gerald had made one thing clear from the start - if you wanted a ride, you had to give him a buck for every mile he drove you. The only exceptions to that rule were Arnold, his best friend, and Phoebe, his best girl.

"Yeah, Gerald?" Arnold stretched his arms high above his head to crack his knuckles, the morning sun shining down on his shaggy blond hair. The drive to school didn't take long, barely ten minutes with traffic, but the two friends knew that these morning drives were key bonding time. A time to chill out, listen to music, and have an easy going chat before the stress of high school consumed their day.

Gerald paused to push his reflective aviator shades higher up on his nose. One time in ninth grade, Phoebe mentioned that she thought aviator shades made guys look sexy. Gerald had gone out and bought a pair the next day. Arnold thought they looked stupid, but Gerald insisted that the shades were indeed sexy. "How long have you and Lila been dating again?"

"Almost two years," Arnold said. He glanced over at his friend, who stared stoically at the road. "Why?"

"No reason, no reason..." Gerald let his voice end on a high pitch, a sure sign that something was on his mind. "Just...how are things with you and Lila?"

The incidents of last night flashed in Arnold's mind, and he winced slightly. "Fine."

Gerald nodded, and began to hum a commercial jingle that Arnold couldn't recognize. The ride continued in silence until Gerald switched the radio on. Obnoxiously loud rock music filled the car and filtered out to the people and cars around them. Men and women dressed in business suits gave Gerald looks of unveiled disgust as they walked to work, as though the volume of his music was to be considered scandalous amongst the already loud city street. But Gerald, with his sleek leather jacket, clean shave, stylish haircut, and aviator shades - he didn't make a move towards the volume control. Arnold, on the other hand, wasn't as cool under pressure. When a grey haired businesswoman served him a full sneer from the sidewalk, Arnold reluctantly dialed the volume back, keeping the music thumping in the background of their drive.

"You worry too much about what other people think, man," Gerald said, cracking a wry grin.

Arnold returned the grin, and ran his fingers through his hair once more - a nervous habit, and a habit of comfort. "Gotta keep that golden boy reputation up, you know?"

Gerald scoffed. "You helped deliver a litter of kittens last weekend. I think you've filled your goodie two shoes quota for the month already."

"Well it was Lila's cat," Arnold said with a smile. "If I didn't help, she would have been mad at me."

"Ha!" This time, Gerald let out a full blown chuckle. "I would pay to see Miss Lila Sawyer get angry. That would be a sight to see- I am ever so upset with you!" Gerald mimicked Lila's high, girlish voice flawlessly. "Why, I am just ever so miffed, I don't know how I will ever forgive you, I am ever so angry!"

Arnold cracked a smile as Gerald laughed. "Lila doesn't get mad," Arnold said. "She just gets upset. Or disappointed. Which is worse, in a way." That had been her true emotion last night - disappointment. She wasn't shocked, she wasn't angry, she was just disappointed in him.

The car rolled to a stop when the convertible hit a red light. As cars whizzed across the intersection before them, Gerald lowered his shades to give Arnold a questioning look. "Alright man, be honest. Something happened with you and Lila, something bad."

"I mean..." Arnold glanced at Gerald, who raised his eyebrows at him. "Yeah. Something did happen."

Gerald returned his attention to the road as the light turned green, and the convertible returned to cruising down the road. "Go on. What happened?"

They would be at the school in just a few minutes, and Arnold knew this was his last chance to get some advice before he had to see Lila. She waited for him at his locker every morning, and he waited at her locker every afternoon. It had been their ritual ever since they started dating. "It was last night," he began. "We were at her house. Her dad was away on a business trip, so Lila suggested we spend the day there. We watched a movie, that cartoon one with the rabbits that she likes. We cooked dinner together, baked cookies, and ate ice cream on the couch...it was a nice night. And then, here's the kicker - after we've washed the dishes and everything, she suggests that instead of going home tonight, I could spend the night with her instead."

Gerald turned to his friend with a broad grin. "Man, did you finally lose your V-card? Is that what you're telling me?"

Arnold held up a finger. "Listen till the end of the story before jumping to conclusions, Gerald."

"Fine, fine!" Gerald grinned, returning his eyes to the road. "So she asked you to spend the night. Then what happened?"

"Well, I said yes." Arnold blushed, thankful that Gerald wasn't watching him at the time. "I said yes, and then we went up to her room. And you know, I'd never been allowed upstairs before, so Lila gave me a tour. Showed me where the bathroom was and stuff. So we get to her room, and she mentions how she's always thought her bed was too big for just one person. Lila has always said that she doesn't want to have sex until the time is right, and now, with her dad away, the house to ourselves, and her inviting me to sleep over, I'm thinking that maybe she's decided that tonight is the right time."

Arnold paused, unsure of how much detail he wanted to divulge, until Gerald smacked him on the arm. "Don't leave me hanging, man. She showed you to her room, you thought it was time for some loving...and then?"

The blond haired boy in the passenger seat groaned. "And then...this is where it gets bad. We're in her room, sitting on the bed talking, and after a while we end up cuddling under the covers. Still fully clothed, mind you. I'm thinking maybe she's just nervous, so I decide to initiate things. We started kissing, and I guess I got too into it...and before I know it she's pushing me away."

"What did you do, smack her ass?" Gerald asked, only half joking.

"No!" Arnold cried. "If you must know...I tried to take her sweater off."

Gerald almost crashed the car, he was laughing so hard. When his chuckles finally died, he was forced to remove the aviator shades to wipe the tears of laughter from his eyes. "Taking her sweater off? That's what turned her off?"

"Listen, alright?" Arnold said, growing frustrated at his friend's amusement at his predicament. "She's upset. Starts talking about respect and misunderstandings, says that she's sorry if she gave me the wrong idea, and that she should have been more clear about her expectations for the night. I said how she had always said she didn't want to have sex till the right time, and that I thought this was the moment we had been waiting for, and I had misunderstood her...and then Lila said that the right moment will be our wedding night."

Gerald violently pulled the car over to the side of the road, making Arnold clutch the dashboard for dear life. After wrenching the gear shift into park, Gerald slammed his hand on the radio's power button, cutting the music short. After the car had been silenced, Gerald tore his sunglasses off to stare at Arnold with wild eyes.

"What the hell?!" Arnold cried, adrenaline pumping through his veins.

"Are you telling me that Lila asked you to marry her?!" Gerald roared. "I don't know whether to slap you or laugh!"

Arnold groaned and slammed his head on the dashboard. "Just...just calm down, okay? I was freaked out when I heard that too, you know? I asked Lila what she meant by that and she said how she wanted to get married after high school, and then she giggled and said how she'll be eighteen in May so I don't have a long wait ahead of me..."

Gerald was shaking his head very slowly, his eyes wide. "This is too much, man. What did you do?"

"I left!" Arnold squeaked, his voice cracking for the first time in a year. He was still barely out of puberty, having inherited his mother's slim build more than his father's muscular physique. His grandfather still teased him about not having a whisper of facial hair. "I went to the bathroom, stayed in there freaking out for a while, then I told Lila that my grandfather had texted saying that I needed to come home. I don't even remember the excuse I made up. Something about my grandma and a cat, I think."

His face was pale, and a sheen of sweat dripped from his brow. Gerald put a strong hand on his friend's shoulder. "Look man, it'll be okay." Arnold knew that it was hollow advice, but he still nodded as though Gerald's words could somehow fix the situation.

"Have you guys talked since then?" Gerald asked.

"No," Arnold said. "She'll probably be at my locker this morning, unless she's really mad at me..."

Gerald paused thoughtfully. "I mean, I could make us late on purpose."

"She has a free period first thing today," Arnold groaned. "There's no escaping, and I can't ditch class."

"Well, then I'm getting back on the road," Gerald responded, moving the gear shift to drive and turning the car back into the flow of traffic. The boys sat in silence until the school came in sight. After the car was parked, Gerald walked Arnold to his locker. As expected, Lila was waiting by Arnold's locker.

"Good luck," Gerald breathed as he left Arnold standing alone. Students crowded the hallway, wasting whatever time they could before class started. All Arnold could focus on was his patiently waiting girlfriend. Lila shot him a sunny smile which he failed to return. She was beautiful as ever, with her auburn hair pulled back into a long braid.

"Hello Arnold," Lila said, and moved to give Arnold's hand a squeeze. "I do hope you slept well. The wind was dreadfully loud last night." She smiled sweetly, and Arnold felt a stab of guilt hit him in the gut.

"I'm really sorry about last night," he said, tripping over his words already. "I didn't mean to leave like I did, and it wasn't anything bad, I mean, I was surprised, yes, but..."

Lila surprised him by kissing his cheek. "Arnold, you are ever so adorable when you are flustered."

Arnold paused. "You're not mad?"

She laughed. "Of course not! I understand why you were surprised though. Most boys aren't quite ready to discuss marriage."

It was as though a hundred pound weight had been removed from his chest. Arnold breathed out a sigh of relief and turned to open his locker with a grin. "I'm glad you understand, Lila. I was just really surprised that you brought it up, I wasn't sure of your expectations."

The bell rang, and Lila put a hand on Arnold's cheek. "I should get to class. And please don't worry about my expectations, as I am ever so sure that we will be ever so happy with our future together." She leaned closer to whisper in Arnold's ear, "And just so that you don't get the wrong idea...I believe that I am looking forward to the wedding night just as much as you are." Her face was rosy with the blush she always got when the topic of sex came up, but she was also giggling. Arnold turned red as well, but his face was one of horror filled shock. Lila walked away before Arnold could reply.

Students departed from the hall quickly until Arnold was left standing alone by his locker. He couldn't remember what his first class was, he was so shocked. Looking forward...to the wedding night? She really did expect them to get married. A text from Gerald woke him from his stupor. Gerald was asking where Arnold was, and said that their math teacher was about to mark him absent.

"Shit!" Arnold cried, and slammed his locker closed. He managed to get to class just as the tardy bell rang, and everyone in the class raised their eyebrows at Arnold being late to class for the first time in at least three years.

"Nice of you to join us, Arnold." The math teacher gave Arnold a stern glare. "Speak to me after class."

Arnold trudged to his seat amongst a roar of whispers as students whispered about the juicy gossip that the golden boy of Hillwood was in trouble. As soon as he took his seat, his phone buzzed with a message.

"How did it go with Lila?" Gerald's text read, and Arnold was about to write a long reply when he noticed that the teacher kept giving him suspicious glances. Arnold quickly typed that he would tell him later, and kept his phone put away for the rest of the lesson. After class, he found himself alone with the stern teacher, who wasted no time in writing Arnold a detention slip.

"I was tempted to give you six days of detention, one for each day," the teacher said. "But considering you've never been late before, I'll let you off with one day. Two hours after school today in the library."

"Yes sir," Arnold muttered, and trudged out of the classroom with a dark cloud over his head. Gerald was waiting for him right outside the door, a loyal friend to the end.

"Detention, huh?" Gerald asked as they walked to their next class. "That sucks, man."

"As if this day could get any worse," Arnold replied grimly.

Gerald wasted no time in getting to the heart of the matter. "So the talk with Lila didn't go well?"

"No, technically it went very well," Arnold said sarcastically. "She isn't mad at me at all! She said that she understands how boys have difficulty talking about marriage, and that she's sure we will be ever so happy with our future together."

"Well, that doesn't necessarily mean she's expecting you to marry her," Gerald said with optimism.

"She said she's looking forward to the wedding night." Arnold turned to Gerald with a panicked expression. "What the hell do I do, Gerald?"

They paused in their walk when they ran into Phoebe. Gerald immediately swooped down to give his girlfriend a firm kiss on the lips, which made her laugh.

"Gerald!" Phoebe giggled, tucking a lock of hair behind her ear. "I have to get to class!" Despite her protests, she still kissed him back.

"Fine," Gerald said with a flirtatious grin. "But I won't let you escape me forever, beautiful."

Phoebe blushed and glanced at Arnold, who felt extremely awkward at the moment. "I'll see you later, sweetie." They shared a brief kiss goodbye, and then continued their separate ways.

"Look man," Gerald said. Now that Phoebe was gone, he was back to his usual cool self. "You're freaked out. I see that. You and Lila have to talk about this. Otherwise she's going to keep thinking you two are having a summer wedding while you stress yourself out over her expectations."

Arnold shook his head. "It won't go well, Gerald. How do you tell a girl that you don't want to marry her, and keep on dating? We like to live in this bubble, avoiding the future for as long as we can, but relationships...either you get married, or you break up. That's it."

Gerald was quiet. "You've spent time thinking about this, huh?"

"About three hours last night," Arnold replied with remorse. "I'm running on four hours of sleep."

The rest of the morning was a blur for Arnold. He could barely keep his eyes open, and his mind was preoccupied with Lila's words and the detention awaiting him after school. By the time lunch arrived, Arnold was ready to go to the nurse's office and sleep through the rest of his classes. But Lila was waiting for him, and he needed to attempt some illusion of normalcy between them.

The cafeteria was packed as usual, and Arnold winced at the oncoming headache he could feel inching its way into his skull as the noise of the crowd grew. His friends were already at their usual table, and Gerald seemed to be telling a joke of some sort. The old gang from elementary school had stayed close, but the group that Arnold ate lunch with were the people he considered good friends. Gerald and Phoebe were at that table, along with Helga, Stinky, Rhonda, Sid, and of course - Lila.

As Arnold approached the table, he could hear Rhonda's voice rise over the others. "Lila dear, I just love your necklace. Wherever did you get it?"

Lila smiled and fingered the silver turtle pendant on her necklace. "Oh it is ever so wonderful, don't you think? Arnold gave it to me for our one year anniversary. I don't usually wear it to school, as it seems ever so fancy for a normal day. But as this is a bit of a special day, I decided to wear it."

Rhonda raised her eyebrows at Arnold. "Oh really? And what makes this a special day?"

Arnold blushed, and a bit of color road to Lila's cheeks as well. "Oh, I'm ever so certain that I don't want to embarrass Arnold, so I won't say." She gave Rhonda a look that very plainly stated that she planned to gush all the details to her later.

"Hey Arnold!" Stinky cried in his usual southern drawl. "I heard you got detention! Now what could you, Arnold, have done to deserve that? On account of you being so sweet tempered, I didn't believe one word of the rumors that you got in a scuffle of some sort, but then again I ain't inclined to believe any bad words about one of my friends, especially one such as morally upstanding as yourself, Arnold."

Sensing that Stinky was about to begin rambling, Sid interjected, "What did you get in trouble for, Arnold?"

"You got detention?" Lila asked, concern clouding her eyes. She put a trembling hand on Arnold's as he slid into a seat next to her. "Are you okay, Arnold?"

Arnold shot her a weak smile before turning back to Sid. "I was late to class this morning, that's all. It's no big deal."

"You've never had detention before," Phoebe commented. "In fact if I remember correctly, you have not received any sort of disciplinary punishment from school since you were in second grade."

"Let's just drop it, okay guys?" Gerald said, raising a hand to quiet any further questions. "He was late to class. It's not much to talk about."

"Did you guys go to the game last night?" Sid asked with excitement, changing the topic without hesitation. "It was great! We beat them by twenty points!"

As the group drifted away to other topics, Arnold found himself awkwardly avoiding talking to Lila by pretending to pay rapt attention to whatever Phoebe was saying about her various AP classes. Senior year was taking a toll on everyone, but Phoebe seemed especially stressed.

"I have way too many college options," Phoebe groaned. "Carnegie Mellon is already sending me letters, but Princeton has a good scholarship and Stanford has someone in the area to interview me next weekend...it's just too much!"

Gerald rubbed her back with a sympathetic smile. "Babe, you'll be fine. Colleges are fighting to accept you before you've even applied."

"Yeah Pheebs," Helga said. "Stop stressing. You'll end up at one fancy university or another, don't worry."

Phoebe rolled her eyes at Helga. "They're not all fancy, you know."

"Of course," Helga said with mock seriousness. "Harvard and Yale aren't fancy at all."

The girls laughed, and Arnold paused for a moment to study Helga. They had all grown up, but Helga had the most radical change. Besides waxing the unibrow away a few years back, she had developed a nice figure and a face that had boys asking her out constantly. Unfortunately for them, Helga always declared that she was too busy to date. She and Lila worked at a local café, and besides that and homework, Helga also played sports year round. She had once told Arnold that staying active helped her manage her anger issues, and Arnold had to admit that she had calmed down more than anyone could have predicted since they were little.

"Arnold?" Lila's sweetly lilting voice pulled him away from his thoughts. "I thought we could go see a movie after my shift tonight."

Arnold returned his attention to his girlfriend, who smiled at him innocently. "Sure," Arnold said. "What movie do you want to see?"

"Oh I saw a trailer for a movie that looked ever so sweet, Arnold. It's about a forest with a skunk for a king, and a chipmunk for a princess...oh it made me laugh ever so much, it looked ever so cute." Lila giggled girlishly, a sound that usually made Arnold laugh with her, but now he could only cringe. He would never admit it to her, but he had come to hate these animated movies with personified animals. Lila had always been very sensitive, and could not stand to see any movies with violence, course language, sex...and Arnold had a love for horror movies. They never saw a movie with a rating higher than PG, and Arnold was getting sick of counting how many situations animated woodland creatures could get thrown in.

"Sounds great," Arnold said, already distracted.

"Then we'll see it tonight!" Lila said with a grin. "Oh Arnold, I'm ever so excited."

"Me too," Arnold replied. Gerald looked over with a frown, seeing Arnold's eyes glazed over with the boredom of a funeral. Arnold and Lila were seen as a perfect couple by most of the school, but those closest to them could see cracks in the foundation already. Even Sid and Stinky, the most separate from the couple, could tell that something was weighing on Arnold's mind. Lila appeared blissfully ignorant as she happily chattered on about the movie.

That afternoon, Arnold entered detention with a surprising amount of nerves. Helga, who got sent here at least once a month, had regaled him with many stories about fights breaking out in detention, kids dealing drugs when the teacher wasn't looking, and worse crimes. Arnold was aware that she was trying to scare him, but he couldn't shake the nerves that made his spine shiver.

"Arnold Shortman," he said stiffly to the teacher in charge of detention that afternoon. "Sent in for being late to first period this morning, detention assigned by Mr. Johnson at 8:47."

The teacher rolled her eyes. "Just sit down. Do homework or something. Stay off your phone, and don't talk." She promptly put earbuds in and started listening to music on her phone.

Arnold let his eyes roam the room, which was empty except for one person - Helga. She lounged in a desk chair, a cherry lollipop in her mouth, her feet propped up on the desk next to her. With a wave of her arm, she beckoned for Arnold to come sit next to her.

"How's it hanging, football head?" she asked casually as he slid into the adjacent desk. "Ready to do some hard time?"

Arnold glanced at the teacher nervously. "Um, Helga...we're not supposed to talk."

She rolled her eyes and jabbed a thumb at the woman in charge of detention. "Oh please. She never takes those earbuds out. As long as we don't disturb her, she doesn't care what we do."

Arnold gave the teacher another look. She looked to be grading papers and completely absorbed by her music. "I guess I'll do homework or something."

"Well that's boring," Helga said in her usual blunt way. "Take a break and just hang out, would ya?"

"Don't you have homework?" he asked, hearing the judgement in his voice.

"Finished it during free period." Helga leaned down to rummage in her bag, and Arnold watched as her long blonde hair fell down in a cascade of loose waves. When she popped up again, she held two lollipops in her hand. "Blueberry or strawberry. Your choice."

Arnold plucked the blue sweet from her hand and popped it in his mouth. "You always carry lollipops around?"

"Only on special occasions," Helga said with a wink.

"And what makes today a special occasion?"

Helga chuckled lowly. "As if you don't know," she said mysteriously.

Arnold furrowed his brow. "I...really don't."

She sighed and popped the sucker out of her mouth. Her lips were stained red from the lollipop. "After lunch, Lila dragged us girls into the bathroom - you know, as we stereotypically feminine ladies do - and told us that she was 'ever so certain' that you were going to ask her to marry you later today. Apparently the two of you had some big romantic talk last night."

Lila was telling people they were getting married? He had thought this was just a fantasy she had that they could talk through. She was serious about them getting hitched, it seemed. Arnold sucked in a slow breath, feeling a dizzy spell approaching. He clutched the desk so hard his knuckles turned white as spots appeared in his vision. A gentle hand on his shoulder startled him out of his panic. He looked up to see Helga looking at him with startled concern.

"Arnold?" she asked quietly. "Are you okay? You look like you're gonna throw up or something."

He shook his head quickly. "I'm fine, just...I need some air."

Helga leaned back in her chair and glanced at the teacher with irritation. "No chance of that. She may be lazy, but she won't let you leave unless you're puking or bleeding all over the place."

"Shit," Arnold muttered.

"Since when do you curse?" Helga asked with a chuckle. Worry still clouded her eyes. Arnold could see that she was genuinely concerned for him, not just waiting to make a joke at his expense. They didn't talk much any more, he realized. Him and Helga, they would hang out almost every day, but never just the two of them. There was always a buffer between them in the form of Lila, Gerald, or Phoebe.

Arnold sighed in defeat. "It's been a rough couple of days, alright?"

Helga observed him with cool eyes, waiting for him to speak. "Do you want to talk about it?" she asked calmly. "We're going to be here for a while."

So far only Gerald knew his situation. Gerald had never betrayed a secret of his, but come to think of it neither had Helga. Oh the rare occasions that they had spoken privately, she had proven herself to be a worthy confidante. "It's about Lila," Arnold admitted with defeat.

"I figured as much." Helga cracked a smile. "Let me guess, she's expecting a summer wedding and you're terrified out of your mind?"

He stared at her in wonder. "You figured that out...shockingly fast."

She shrugged. "What can I say, I'm observant. Lila said you two had a big romantic talk about marriage and life and love last night, but you were pale as a ghost all through lunch."

"We did talk last night," Arnold said. "She implied that she was expecting us to get married after high school...and then I left." He admitted the last part with his head hanging low.

"Wait, you left?" Helga raised her eyebrows. "Does that mean you don't want to marry her?"

"I don't know!" Arnold exclaimed, wringing his hands in frustration. "I'm seventeen, it's my last year of high school...I'm too young to think about marriage! I want to go to college, start a career, and have my life figured out before I get to marrying."

Helga paused to remove the sucker from her mouth. "Alright, hypothetical situation. Let's say you were at that point in your life. You've been through college, you have a good job, everything in your life is figured out. Then Lila, your girlfriend of almost two years, brings up marriage. Would you want to marry her?"

He stared at the floor as the realization hit him. "I don't know."

"You don't know?" Helga asked critically. "You've been dating this girl for two years, had a crush on her since elementary school, and you don't know if you can see a real future with her?"

"I'm only seventeen!" Arnold cried. "I don't know what college I want to spend the next four years at, let alone what girl I want to spend the rest of my life with!"

"Then just tell her that," Helga responded patiently. "Sit Lila down and tell her that you think she's great but you aren't ready to get married yet. You can have a perfectly normal relationship without rushing into marriage, you know. She has to understand that you're in high school, and in high school you just date people. There doesn't have to be the ultimatum of marriage or break up hanging over your heads."

"It's not just that," Arnold said quietly. "The more I think about it...marrying Lila, having a future with her...I realize that I can't even see us dating after high school."

"Woah," her words were only a breath of air in the quiet classroom. "Are you going to break up with her?"

Arnold shook his head. "No, I don't want to upset her."

"Arnold," Helga said, a hint of humor in her. "Everything upsets Lila." She waited for him to protest, to defend Lila like he always did. Instead, he chuckled.

"You got that right," he said with a touch of wry sarcasm. "Cursing, loud music, the sight of vodka, rapping, horror movies, sick animals..." The list turned into an angry rant as he continued. "Dinner after seven o'clock, roller coasters, dairy, nuts, shellfish, basically anything you could possibly order at a restaurant..."

"Arnold," Helga reached to stop him just as his rant reached its climax. His anger was unexpected, a boiling pot that was about to overflow.

"Reality TV, heights, deep water, even taking her fucking sweater off!" He was out of his breath, and red in the face. A sheen of sweat had appeared on his brow, and his fists were continuously clenching and stretching. Helga observed the boy before her. Shaggy blond hair with bangs that were pushed back to hang haphazardly around his head, shaved short in the back. A sweater she remembered Lila having given him for his birthday, jeans, and beat up sneakers. Dark circles hung loosely under his eyes, and suddenly the boy before her looked as though he had aged a decade in the last twenty four hours.

"You seem bit upset," Helga said daintily.

Arnold took a slow breath. "Sorry," he muttered. "I guess I needed to vent."

"So Lila gets upset by things," Helga said, attempting to pass off his complaints casually. "She's sensitive. But you two get along perfectly, you never fight."

"We never fight because we do whatever she wants," Arnold said. "She doesn't like the movies I like, so we always go and see the cute animal films she loves. She won't eat meat, she's lactose intolerant, allergic to nuts, deathly allergic to shellfish...I try to find restaurants that can accommodate her but every time we go out, we end up at the same restaurant because that's the only place she wants to go to. She thinks it's deadly to go out at night, that the subway is filled with gangs, and that drug dealers are hanging around every alley."

"She does realize this is Hillwood, right?" Helga said with a chuckle. "It's a city. Yeah there are gangs and drugs and stuff, but if you're smart then you can keep yourself safe. I've never run into any trouble."

Arnold laughed. "Yeah, because you walk around with a scowl on your face and a set of brass knuckles on your hands."

"I do not, you ass!" She laughed, and Arnold felt himself relax for the first time all day.

"Remember Gerald's birthday party last year?" Arnold asked.

She nodded with a smile. "Man that was fun...didn't he have a mechanical bull?"

"No, you were drunk and tried to make Harold give you a piggy back ride." They laughed at the memory. Gerald was home alone for the weekend and took the opportunity to throw one of the most epic parties Hillwood High had ever seen. Lila had declined to attend the party, leaving Arnold free to go as wild as he wanted to.

"I remember you got so high," Helga laughed, "That you startled rambling on about jungle tigers for half an hour."

Arnold's smile turned somber. "Lila was so upset with me after that party. On Monday, she came up to me crying about how I had betrayed my moral compass, that I wasn't the guy she had thought I was..."

"Geez," Helga said, raising her eyebrows. "What did you do?"

"I promised her I'd never smoke or drink again." Arnold shook his head in frustration. "I didn't go to Gerald's birthday party this year because Lila said that if I went, she couldn't trust that I wouldn't drink or smoke."

Helga shook her head. "That's intense. I knew she was sheltered, but I didn't think it affected things between you two much."

Arnold paused. "If I tell you something, will you keep it to yourself?"

"Scout's honor," Helga said with a smirk. "What happens in detention, stays in detention."

He sighed. "We've been dating for almost two years, and we've never had sex."

"That's not a bad thing," Helga said. "A lot of people don't want to go all the way yet."

"I know, but...we've never done anything more than kiss." He ran a hand through his hair, looking frustrated and awkward.

"Making out can be fun," she encouraged. "Nothing wrong with just messing around."

"Not making out," he said. "Just kissing. Simple pecks on the lips, nothing lasting more than three seconds. Last night, I thought she wanted to go further, and when I tried to take her sweater off, she freaked out. I thought she was going to cry!"

Helga raised her eyebrows. "I'm not sure what to say, football head."

"What can anyone say?" Arnold said bitterly. "This relationship only works because everything is dictated by Lila's needs."

"So is that it then?" Helga asked quietly. "Are you going to dump her?"

Arnold sucked on his lollipop thoughtfully, weighing his options. "If I do, she'll cry. No matter what I say, everyone will see me as the bad guy."

"And if you don't," Helga quipped. "You'll have to marry her."

He groaned a heavy sigh. "Not breaking up would just be delaying the inevitable, it seems. What do you think?"

Helga held up her hands. "Oh no, I'm not going to give you advice. I don't want to be the girl who told you to break up with your girlfriend. Enough people hate me already. Let's not add home wrecker to my list of detestable attributes." She chuckled wryly, though Arnold could see the hurt in her eyes. Helga tried to be nice, she really did, but most people couldn't see past her constant scowl and tough girl act. Her friends knew she was sweet at heart, but it took time to chip past her armor of sarcasm and violent threats.

"Don't worry," Arnold said with a gentle smile. "What happens in detention stays in detention, remember? You've listened to me vent, you know the situation. So what would you do if you were in my shoes?"

She stared off into space. After a moment, she snapped back to reality and looked at him with a strangely distant expression. "Remember when I dated Harold?"

Arnold chuckled. "Yeah. Most mismatched couple of all time."

"Well, that relationship was pretty messed up." She spoke with a frosty chill to her voice, eyes still distant and darkening. Arnold could tell that this was a story she hated telling. "It was late in freshman year. He had dated like, three or four girls by then, being a sports guy who liked partying. I had never been in a relationship before. I was constantly terrified that he was going to dump me. So I tried to be the perfect girlfriend. I made signs to cheer him on at his games, and sat through his practices. I remember sitting with the other guys' girlfriends, and hearing them talk about sex and parties and how stupid they thought school was...we had nothing in common. It was lonely. I went to the parties Harold wanted to go to, we went to whatever movie he wanted to see, whatever restaurant he wanted to eat at...kind of like you and Lila, now that I think about it."

"He never asked you what you wanted to do?" Arnold asked critically.

Helga nodded, her eyes still staring at a certain spot on the wall. "Yeah, he did. He asked me that a lot. And I just kept remembering him teasing me about being bossy and mean when we were little, and how I didn't want him to think of me like that so I would just smile and say I liked doing the stuff he liked. It wasn't too bad, just going along like that. But at a certain point, I realized that I didn't even like Harold that much anymore. He was a good guy to hang out with, but there wasn't a romantic connection between us anymore. I think I just liked having a boyfriend. Knowing that there was someone who really liked me, who thought I was special." She turned to Arnold with a sad smile. "You chased Lila for years. You want my opinion? From where I'm standing, it looks like you've been so focused on getting Lila to be with you, you forgot to put yourself first."

Arnold winced. "It seems selfish. Putting yourself first, I mean."

"No matter how much you care for another person," Helga said, gazing at him with incredible intensity, "Your health and happiness comes first. Never forget that."

He gave a small, awkward laugh. "Seems a bit wise for a seventeen year old girl to be saying."

She gave a half smile with sad, deadened eyes. "Five relationships in three years teaches you a thing or two."

Arnold remembered the relationships she spoke of. First it was Harold. That lasted about four months. Then she dated Wolfgang, a tough guy who seemingly forced an alarming amount of innocence out of Helga's persona. They were together for maybe seven months. Wolfgang had dumped her. Rumor was that she refused to have sex with him. She dated a guy in college for a couple months, but had never said much other than that it was a summer fling, nothing more. Brainy was boyfriend number four, the total opposite of Wolfgang. He was quiet and awkward, and no one could quite understand why they dated, but Arnold remembered seeing Helga giving Brainy the warmest smiles he could ever remember seeing from her. They were together for all of junior year, and would probably still be together if his family hadn't moved to Europe.

The latest boyfriend was Iggy. He was constantly partying, and brought her along for the ride. Arnold remembered seeing Helga hungover at school from full weekend-long parties multiple times during the three months that she and Iggy were together. They had only broken up a few weeks ago, and she had been the one to dump him. She said that they were too different, and that she needed to focus on her future instead of getting high with strangers. But Phoebe had let it slip to Gerald that Helga had discovered Iggy cheating on her multiple times, and of course Gerald had told Arnold. Meanwhile, Arnold had been single until Lila agreed to become his girlfriend at the homecoming dance in sophomore year.

The school bell rang, and the teacher at the desk pulled out an earbud with an expression of pure irritability. "Detention is over. Leave so I can lock up."

Helga and Arnold quickly slung their backpacks over their shoulders and strode out of the room. They walked through the hallways in silence, not sure what note their unexpectedly intimate conversation should end on. When they stepped out of the building, Arnold was immediately distracted by the beeping of a car horn. He turned to see Gerald sitting in his car nearby, having waited to give Arnold a ride home. No doubt he was hoping to find out what Arnold planned to do about Lila.

"Well," Helga said breezily. "I have to get to work."

Arnold nodded awkwardly. Now that the quiet privacy of detention was gone, the air was weighed down with all the things left unsaid. He wanted to find out the details of her past relationships, to learn what made her look so sad and bitter when she thought about the guys she had dated. He wanted to tell her all the little stories about him and Lila, the things that he had always wanted to rant about and be told that he was right to be frustrated, that it wasn't selfish to have needs.

"Maybe we could hang out this weekend," Arnold said quickly.

Helga paused. "Um...maybe."

"We could go to the park or something," he offered. "I'll text you, okay?"

She gave an uncertain smile. "Yeah." The smile relaxed. "Yeah, I'd like that."

Arnold grinned. "Cool."

The two stood there in silence for a moment, just smiling at each other. Finally, Helga gave a little wave and turned to go. "See ya, football head."

"Later, Helga." Arnold walked towards Gerald's car with a smile stuck on his face, keeping his head down so Gerald wouldn't tease him. As soon as he sat down in the convertible, Gerald lowered his aviator shades to raise his eyebrows questioningly.

"So how was detention with Pataki?" he asked.

Arnold shrugged. "Fine."

"Just fine?" Gerald threw the car into reverse and began backing out of his space to leave the parking lot. "What did you guys do?"

"Did homework," Arnold lied easily. "Hung out, talked a bit."

Gerald nodded and moved out onto the road. After a less than a minute of silence, Gerald let the obvious question burst free. "So what are you going to do about Lila?"

Arnold sighed with a knowing smile. "We're supposed to go to a movie after she gets off work today. I'm going to talk to her before we get to the theater."

"Are you going to break up with her?" Gerald asked. His voice was kept casual and light, but Arnold could see his fingers tapping nervously on the steering wheel.

"We're just going to talk," Arnold said carefully. As much as he trusted Gerald, he knew that his love struck friend ended up repeating everything to Phoebe. She generally knew what to keep to herself, but Arnold would rather not take the chance with a situation as delicate as this. "I'm going to confront the marriage issue and see if we can work it out."

"And if you can't?" Gerald pressed. "What then?"

Arnold rolled his eyes at the anxiety creeping into Gerald's voice. As cool as Gerald was, he had a tendency to get emotionally caught up in these social dramas. "If we can't work it out, then hopefully we can stay friends."

"Good luck with that," Gerald said with a chuckle. "Staying friends with an ex is never easy, especially when you've been dating for so long."

"I know," Arnold said. "I'm not saying we'll be best friends, but if we could at least stay civil, that would be nice."

Later that night, Arnold stood outside Café Hillwood with sweaty palms and a set of wildly jangling nerves. Breaking up was easy enough to hypothesize about, but confronting the situation was much harder. He would be breaking the heart of the sweetest, kindest girl in Hillwood. Many would see him as a soulless monster. But those who mattered, his true friends, would know the truth and stick by him. At least, he hoped they would.

Lila stepped out of the café wearing her uniform, a black skirt and a white company shirt, with a blue cardigan thrown on. "Arnold!" she exclaimed with a smile. She stood up on her tip toes to kiss his cheek in greeting before stepping back to give him a sweet smile. "I'm ever so excited for our date," she said, fingering her necklace.

They began the walk to the movie theater. Arnold felt his heart thumping wildly in his chest as Lila slipped her hand into his and gave it a squeeze. The theater was less than a mile away, so he knew he would have to start talking soon. "Lila," he said awkwardly, uncertain how to begin the speech he had been going over in his head for the last hour. "I've been thinking a lot about last night, about what you said."

"I'm ever so glad to hear that, Arnold." Lila gave him a sunny smile.

He gulped nervously. "Uh, yeah. Just to be clear - I'm fine with you not wanting to have sex until you're married. That's your decision."

Lila blushed at his mention of sex. "Well I'm ever so certain that I wouldn't want to share something that intimate with anyone except the man I had promised to spend my life with."

"And that's fine!" Arnold heard his voice crack from nervousness. "Perfectly fine! It's just...I don't know if I can be that man."

Lila stopped walking and turned to Arnold with sadness already enveloping her beautiful face. "What ever do you mean?"

"We just want different things," Arnold said, hating how cliche he sounded already. "You want to get married after high school and start a family. I want to go to university and start a career. I'm not going to be ready for marriage for a long, long time."

Her face was solemn as she slowly released Arnold's hand from her own. Her gaze was glued to the gritty sidewalk under their feet. "Are you breaking up with me?" she asked quietly.

Arnold hesitated. Was this really what he wanted? To end a two year relationship because he wasn't sure that he could see a feasible future? His mind flashed back to his conversation with Helga. For him and Lila to work as a couple, they would have to completely reevaluate their relationship. Everything would have to change. But she wouldn't be happy with that, and he wouldn't be either. "I think I am," he said quietly. The speech he had planned was gone. All he could do now was be honest. "Last night, I was scared. I didn't realize you expected us to get married...I had never even thought about that possibility. I thought about just saying that I didn't want to get married yet, and to just keep dating for a while, but that wouldn't be fair to either of us."

"We don't have to get married right after high school," Lila said desperately. "I can wait!"

"It's not just that." Arnold looked away, unable to meet her gaze. "I know people like to say that we're a perfect couple, but we're not. We don't have a lot of common interests, our plans for the future are completely opposite...I just don't think this is going to work long term."

"What did I do wrong?" Lila asked, tears welling up in her big brown eyes. "I'm ever so certain that I did my best to be good to you, Arnold. What did I do wrong?"

Arnold paused. Sometimes, honesty wasn't the best policy. "You are amazing," he said as sincerely as he could. "Lila, you're an amazing girl. You're kind, smart, funny, honest...anyone would be lucky to date you."

Lila began to cry bitterly. Arnold hesitated, unsure whether he should reach out to comfort her or not. Once she had composed herself, Lila looked up at Arnold with her lip stuck out in a stubborn pout. "Then why do you not want to be with me anymore? We had such a nice time last night...what happened?"

He sighed. She wasn't going to let him off the hook on this one. "Once you brought up the possibility of marriage, I started thinking about our future together...and I realized that I couldn't see one. I could see us continuing with what we have now - our usual Saturday date nights, dinner with your dad on Sunday, meeting you at your locker before you have to go to work...but that's it. I can't see you as anything but my high school girlfriend. And the more I thought about that, the more I realized how different we are. I realized that the only reason this relationship works is because we do whatever you want."

"Are you saying I'm controlling?" A touch of bitter insult touched Lila's dulcet tones. "Selfish? Manipulative?"

"No!" Arnold held up his hands to stop her. "Lila, you are none of those things. It's my fault, really. I was so happy that we were finally dating that I just got in the habit of doing whatever I could to please you. Going to the movies you like, eating at the restaurants you prefer...it wasn't bad, but after a while I started craving variety. But whatever I suggested was totally opposite to your preferences, so after a while I gave up."

"We can change," Lila said quickly. "I can change!"

"We tried that, remember?" Arnold said with a sad, gentle smile. "We went to see an action flick and you got upset by the violence and language in it. When the two main characters started making out, you said we should leave. I took you to my favorite steakhouse and got you a veggie burger, but you still got upset by the smell of meat around you. Lila, you shouldn't have to change for me. You should change because you want to, not because you feel like you have to to make your boyfriend happy."

She nodded, slowly beginning to understand. "I see your point," she admitted. "I guess this is it, then."

"Yeah." Arnold put out a hand for her to shake. "Friends?" he asked with a forced smile.

Lila looked up with a sad smile. "I'd like that." They shook hands, and that was it. Arnold and Lila, the "perfect couple of Hillwood" were over.

"Do you still want to go see that movie?" Arnold asked, knowing it was a token gesture.

She shook her head and pulled her cardigan tighter around her body. "No, I think I'll just go home. I'll see you tomorrow, Arnold." She walked away quickly, her long auburn braid waving back and forth behind her. Arnold looked after her with a sad smile.

As he walked home, Arnold couldn't help but feel carefree. It was as though a weight had been lifted off his conscious. He had been honest but kind, and Lila didn't seem too upset with him. Looking back, he could see all the times he had held himself back in an effort to keep the relationship with Lila peaceful. Helga was right - you could learn a lot from relationships. Helga was right about a lot of things. With a smile, Arnold pulled out his phone to text a certain blonde.

"Hey," he typed. "Let's hang out this weekend."

He received a reply within a minute. "What about Lila? I'm not going to be your rebound, Bucko."

"Don't worry about that," he replied. "I just want to hang out with my friend."

A few minutes passed before she sent her reply. "Fine. But don't get any weird ideas, football head."

Arnold grinned and typed the phrase he knew she loved to hear from him. "Whatever you say, Helga."

* * *

 **A bit of an expected ending phrase, but I enjoy the banter that those two have kept between them for years. The breakup scene was probably the hardest part to write, as Arnold had to be honest but kind. Will Arnold and Helga start dating? Will he and Lila stay friends? Only time will tell, though there probably won't be a sequel to this. Anyway, leave reviews and tell me what you think!**


	2. Character Descriptions

**Here are the characters' physical descriptions, in order of appearance. These are to be used for a reference in how I imagine the characters appearing during the story. If you imagine them differently, that's perfectly fine.**

* * *

 **Arnold**  
Height: 5'10"  
Build: slim, quite strong but without much visible muscle  
Hair: cut short on the sides and left long and unruly on top, creating the illusion of a longer, less football shaped head  
Makeup and Piercings: no piercings, but he sometimes uses foundation to cover pimples  
Standard Outfit: blue jeans, sneakers, and a brown sweater with a blue plaid button up shirt underneath, the sleeves usually rolled up

 **Gerald**  
Height: 6'1"  
Build: sleek muscles, slim, healthy, and strong  
Hair: box fade, always freshly shaved (similar to a shorter version of the cartoon's haircut)  
Makeup and Piercings: pierced lobes  
Standard Outfit: stylish black leather jacket, aviator shades, fitted dark blue jeans, muted red sweater, fashionable sneakers

 **Lila**  
Height: 5'5"  
Build: average, not very fit  
Hair: auburn, almost down to her waist when loose. Just about always worn pulled back into a single thick braid  
Makeup and Piercings: nothing except chapstick  
Standard Outfit: knee length yellow dress with white flower designs, a blue cardigan, white flats

 **Phoebe**  
Height: 5'1"  
Build: petite and slim with a buxom chest  
Hair: cut at shoulder length, and often pulled back with silver barrettes or a headband  
Makeup and Piercings: standard lobe piercings, wears mascara and lipgloss  
Standard Outfit: a knit blue dress, denim jacket, and black combat boots

 **Helga**  
Height: 5'8"  
Build: slim and wiry, with subtle curves, is strong due to athletics  
Hair: long and wavy, down to the middle of her back. Often pulled back into a pony tail, accentuating her strong cheekbones  
Makeup and Piercings: cartilage piercing on her right ear, wears dark eye makeup  
Standard Outfit: black jeans, fitted pink tank top, white converse sneakers and a black cropped leather jacket

 **Rhonda**  
Height: 5'2" (5'5" when wearing heels)  
Build: slim, fit, curvaceous, known to have one of the best figures in school  
Hair: long and black, curled glamorously every day  
Makeup and Piercings: two piercings on each ear, black eyeliner and red lipstick, loves to wear gold hoop earrings  
Standard Outfit: a black dress and bright red heels, with lots of jewelry. Carries a large red purse instead of a backpack

 **Sid**  
Height: 5'8"  
Build: slim, he isn't very athletic or fit  
Hair: shaggy layers trimmed to be styled cleanly but stylishly  
Makeup and Piercings: multiple ear piercings, plus a silver eyebrow ring  
Standard Outfit: a black leather jacket, tight black jeans, a collared white shirt and his standard white boots. He likes to emulate the 80's gangster look

 **Stinky**  
Height: 6'5"  
Build: lanky, with a long face and long, gangly limbs  
Hair: buzzed short, with a bit of unruly tuft hanging over his forehead  
Makeup and Piercings: none  
Standard Outfit: beat up blue jeans, a plain green shirt, and old sneakers. His style has not changed much over the years

* * *

 **Feel free to use these descriptions for your own stories or drawings if you want, I have no real claim to them. Hope you enjoyed the story!**


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